Novel herbicides

ABSTRACT

Compounds of formula I  
                 
 
     wherein the substituents are defined as in claim 1, as well as the agronomically acceptable salts, isomers and enantiomers of these compounds, as well as the agronomically acceptable salts/N-oxides/isomers/enantiomers of these compounds, are eminently suitable for use as herbicides.

[0001] The present invention relates to novel herbicidally active benzoyl derivatives, to processes for their preparation, to compositions comprising said compounds, and to the use thereof for controlling weeds, in particular in crops of cultivated plants or for inhibiting plant growth.

[0002] Benzoyl derivatives with herbicidal activity are described for example in U.S. Pat. No. 5,094,685. Now, novel benzoyl derivatives with herbicidal and growth-inhibiting properties have been found.

[0003] The objects of the present invention are thus compounds of formula I

[0004] wherein

[0005] X is L₁-Y₁-R₄, L₂-Y₂-L₃-Y₃-R₅ or L₄-Y₄-L₅-Y₅-L₆-Y₆-R₆;

[0006] L₁,L₂, L₃, L₄, L₅, L₆, independently of one another, signify C₁-C₆-alkylene, which may be substituted by C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy, C₂-C₆-alkenyl or C₂-C₆-alkynyl; or C₃-C₆-alkenylene, which may be substituted by C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy, C₂-C₆-alkenyl or C₂-C₆-alkynyl; or C₃-C₆-alkynylene, which may be substituted by C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy, C₂-C₆-alkenyl or C₂-C₆-alkynyl;

[0007] Y₁, Y₃, Y₆, independently of one another, signify oxygen, sulphur, SO, SO₂, NR₇, OC(O), NR₈SO₂ or OSO₂;

[0008] Y₂, Y₄, Y₅, independently of one another, signify oxygen, sulphur, SO, SO₂, NR₉, OC(O) or NR₁₀SO₂;

[0009] R₇, R₈, R₉ and R₁₀, independently of one another, signify hydrogen or C₁-C₆-alkyl;

[0010] R₁ and R₂, independently of one another, signify halogen, cyano, nitro, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-dialkylaminosulphonyl, C₁-C₆-alkylaminosulphonyl, C₁-C₄-alkylsulphonylamino, C₁-C₆-halogenalkoxy, OSO₂-C₁-C₄-alkyl, C₁-C₆-halogenalkylthio, C₁-C₆-halogenalkylsulphinyl, C₁-C₆-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl;

[0011] R₃ signifies hydrogen, C₁-C₄-alkyl or halogen;

[0012] R₄, R₅ and R₆, independently of one another, signify hydrogen, C₁-C₆-alkyl, which may be substituted by the group A₁; C₃-C₇-cycloalkyl, which may be substituted by the group A₂; C₃-C₇-cycloalkyl, which may be interrupted by 1 to 2 oxygen atoms, sulphur or NR₁₁; C₂-C₆-alkenyl, which may be substituted by the group A₃; C₃-C₆-alkynyl, which may be substituted by the group A₄; C₃-C₇-cycloalkyl-C₁-C₄-alkyl, whereby the cycloalkyl group may be interrupted by 1 to 2 oxygen atoms, sulphur or NR₁₂; benzyl or phenyl which may in turn be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, cyano, nitro, C₁-C₄-halogenalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-dialkylamino, C₁-C₄-alkylcarbonyl, C₁-C₄-dialkylaminosulphonyl or NR₁₃-CO-R₁₄;

[0013] R₁₁ and R₁₂, independently of one another, signify hydrogen or C₁-C₄-alkyl;

[0014] R₁₃ and R₁₄, independently of one another, signify hydrogen or C₁-C₄-Alkyl;

[0015] A₁, A₂, A₃, A₄, independently of one another, are hydroxy, formyl, COOH, C₁-C₆-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, OSO₂-C₁-C₄-alkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkylaminocarbonyl, C₁-C₆-dialkylaminocarbonyl, nitro, halogen, cyano, C₁-C₄-alkoxyhalogen, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or phenyl, whereby the phenyl group may in turn be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, cyano, nitro, C₁-C₄-halogenalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-dialkylaminosulphonyl or NR₁₅-CO-R₁₆;

[0016] R₁₅ and R₁₆, independently of one another, signify hydrogen or C₁-C₄-alkyl;

[0017] Q is the group Q₁

[0018] wherein R₃₉ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-dialkylamino, COOH, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁-C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano; V is C₁-C₄-alkylene, oxygen, sulphur, SO or SO₂;

[0019] R₁₇, R₁₈, R₁₉, R₂₀, R₂₁ and R₂₂, independently of one another, signify hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkylaminosulphonyl, C₁-C₄-halogenalkyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkoxy, cyano, nitro, halogen or phenyl,

[0020] q is 1 or 2;

[0021] or Q is the group Q₂

[0022] wherein

[0023] R₂₃ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-dialkylamino, COOH, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylthio, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphinyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphonyl, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁-C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano;

[0024] R₂₄ and R₂₅, independently of one another, signify hydrogen, hydroxy, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkylaminosulphonyl, C₁-C₄-halogenalkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, amino, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkyl-S(O)₂O, C₁-C₄-halogenalkylthio, C₁-C₄-halogenalkylsulphinyl, C₁-C₄-halogenalkylsulphonyl, C₁-C₄-halogenalkyl-S(O)₂O, C₁-C₄-alkyl-S(O)₂NH, C₁-C₄-alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or R₂₄ and R₂₅ together form a C₂-C₆-alkylene bridge,

[0025] R₂₆ signifies hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl or phenyl, which may in turn be substituted by C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, amino, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkyl-S(O)₂O, C₁-C₄-halogenalkylthio, C₁-C₄-halogenalkylsulphinyl, C₁-C₄-halogenalkylsulphonyl, C₁-C₄-halogenalkyl-S(O)₂O, C₁-C₄-alkyl-S(O)₂NH, C₁-C₄-alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano;

[0026] or Q is the group Q₃

[0027] wherein

[0028] R₂₇ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₈-alkoxycarbonyloxy, C₁-C₆-dialkylamino, COOH, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylthio, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphinyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphonyl, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁-C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano;

[0029] R₂₈, R₂₉ and R₄₀, independently of one another, signify hydrogen, hydroxy, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkylaminosulphonyl, C₁-C₄-halogenalkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, amino, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkyl-S(O)₂O, C₁-C₄-halogenalkylthio, C₁-C₄-halogenalkylsulphinyl, C₁-C₄-halogenalkylsulphonyl, C₁-C₄-halogenalkyl-S(O)₂O, C₁-C₄-alkyl-S(O)₂NH, C₁-C₄-alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or R₂₈ and R₂₉ together form a C₂-C₆-alkylene bridge,

[0030] R₃₀ signifies C₁-C₆-alkyl, which may be substituted by a group A₅; C₂-C₆-alkenyl, which may be substituted by a group A₆; C₂-C₆-alkynyl, which may be substituted by a group A₇; A₅, A₆ and A₇, independently of one another, are hydroxy, formyl, COOH, C₁-C₆-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, OSO₂-C₁-C₄-alkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkylaminocarbonyl, C₁-C₆-dialkylaminocarbonyl, nitro, halogen, cyano, C₁-C₄-alkoxyhalogen, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or phenyl, whereby the phenyl is in turn substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, cyano, nitro, C₁-C₄-halogenalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-dialkylaminosulphonyl or NR₃₁-CO-R₃₂;

[0031] R₃₁, R₃₂, independently of one another, signify hydrogen or C₁-C₄-alkyl;

[0032] or Q is the group Q₄

[0033] wherein

[0034] R₃₃ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylthio, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphinyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphonyl, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁-C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano;

[0035] W is oxygen, sulphur, SO, SO₂, NR₃₈ or C═O;

[0036] R₃₈ signifies hydrogen or C₁-C₆-alkyl;

[0037] R₃₄, R₃₅, R₃₆ and R₃₇, independently of one another, signify hydrogen, hydroxy, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkylaminosulphonyl, C₁-C₄-halogenalkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, amino, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkyl-S(O)₂O, C₁-C₄-halogenalkylthio, C₁-C₄-halogenalkylsulphinyl, C₁-C₄-halogenalkylsulphonyl, C₁-C₄-halogenalkyl-S(O)₂O, C₁-C₄-alkyl-S(O)₂NH, C₁-C₄-alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or R₃₄ and R₃₅ together form a C₂-C₆-alkylene bridge, as well as agronomically acceptable salts, isomers and enantiomers of these compounds.

[0038] The invention similarly relates to the salts that may be formed by the compounds of formula I, especially those compounds of formula I in which R₂₃, R₂₇, R₃₃ and R₃₉ are hydroxy, with amines, alkali metal bases and alkaline earth metal bases, or quaternary ammonium bases.

[0039] Of the alkali metal hydroxides and alkaline earth metal hydroxides as salt-forming components, the hydroxides of lithium, sodium, potassium, magnesium or calcium are notable, especially those of sodium or potassium.

[0040] Examples of amines that are suitable for ammonium salt formation may be both ammonia and primary, secondary and tertiary C₁-C₁₈-alkylamines, C₁-C₄-hydroxyalkylamines and C₂-C₄-alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methyl-iso-propylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, di-n-butylamine, di-n-amylamine, di-iso-amylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, iso-propanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, di-butenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-n-butylamine, tri-iso-butylamine, tri-sec.-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines such as pyridine, quinoline, iso-quinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines such as anilines, methoxyanilines, ethoxyanilines, o,m,p-toluidines, phenylenediamines, benzidines, naphthylamines and o,m,p-chloroanilines; but especially triethylamine, iso-propylamine and di-iso-propylamine.

[0041] The alkyl and alkylene groups present in the definitions of the substituents may be straight-chained or branched and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec.-butyl, iso-butyl, tert.-butyl, pentyl and hexyl, as well as the branched isomers thereof. Alkoxy, alkenyl, alkenylene, alkynyl and alkynylene groups are derived from the said alkyl groups. The alkenyl, alkenylene, alkynyl and alkynylene groups may be mono- or multi-unsaturated.

[0042] Halogen normally signifies fluorine, chlorine, bromine or iodine. The same applies also to halogen in conjunction with other definitions such as halogenalkyl or halogenphenyl.

[0043] Halogenalkyl groups preferably have a chain length of 1 to 6 carbon atoms. Halogenalkyl is for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

[0044] Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is for example methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, iso-butoxy, sec.-butoxy and tert.-butoxy as well as the isomers pentyloxy and hexyloxy; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl signifies for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec.-butoxycarbonyl or tert.-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl. Halogenalkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Halogenalkoxy is e.g. fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Alkylthio groups preferably have a chain length of 1 to 6 carbon atoms. Alkylthio is for example methylthio, ethylthio, propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec.-butylthio or tert.-butylthio, preferably methylthio and ethylthio. Alkylsulphinyl is for example methylsulphinyl, ethylsulphinyl, propylsulphinyl, iso-propylsulphinyl, n-butylsulphinyl, iso-butylsulphinyl, sec.-butylsulphinyl, tert.-butylsulphinyl; preferably methylsulphinyl and ethylsulphinyl.

[0045] C₃-C₇-cycloalkyl, which is interrupted by oxygen, is for example oxiranyl, oxetanyl, tetrahydrofuranyl, dioxolanyl, oxacyclohexyl, dioxacyclohexyl, oxacycloheptyl or dioxacycloheptyl.

[0046] C₃-C₇-cycloalkyl-C₁-C₃-alkyl, which may be interrupted by oxygen, is for example oxiranylmethyl, oxetanyl-ethyl, tetrahydrofuranyl-n-propyl, dioxolanyl-C₁-C₃-alkyl, oxacyclohexyl-C₁-C₃-alkyl, dioxacyclohexyl-C₁-C₃-alkyl, oxacycloheptyl-C₁-C₃-alkyl or Dioxacycloheptyl-C₁-C₃-alkyl.

[0047] Alkylsulphonyl is for example methylsulphonyl, ethylsulphonyl, propylsulphonyl, iso-propylsulphonyl, n-butylsulphonyl, iso-butylsulphonyl, sec.-butylsulphonyl or tert.-butylsulphonyl; preferably methylsulphonyl or ethylsulphonyl Alkoxyalkoxy groups preferably have a chain length of 2 to 4 carbon atoms.

[0048] Examples of alkoxyalkoxy are: methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy or butoxybutoxy.

[0049] Alkylamino is for example methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines. Dialkylamino is for example dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino. Preference is given to alkylamino groups with a chain length of 1 to 4 carbon atoms. Alkoxyalkyl groups preferably have 2 to 4 carbon atoms. Alkoxyalkyl signifies for example methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. Alkylthioalkyl groups preferably have 2 to 4 carbon atoms. Alkylthioalkyl signifies for example methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl. The cycloalkyl groups preferably have 3 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Phenyl, even as part of a substituent, such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl or phenoxyalkyl, may be present in substituted form.

[0050] Preference is given to compounds of formula I, in which R₁ and R₂, independently of one another, signify halogen, cyano, nitro, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-dialkylaminosulphonyl, C₁-C₆-alkylaminosulphonyl, C₁-C₆-halogenalkoxy, OSO₂-C₁-C₄-alkyl, C₁-C₆-halogenalkylthio, C₁-C₆-halogen-alkylsulphinyl, C₁-C₆-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl and

[0051] R₃₃ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-dialkylamino, COOH, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylthio, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphinyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphonyl, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁ -C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano.

[0052] Further preferred compounds of formula I are characterised in that Q is Q₁ or Q₂, whereby in the group Q₂, R₂₄, R₂₅ and R₂₆ are preferably hydrogen or C₁-C₆-alkyl. R₂₃ and R₃₉ denote hydroxy in particular. Also notable are those compounds of formula I, in which X is L₁-Y₁-R₄. Of this group, the compounds in which L₁ signifies methylene are preferred. In a further preferred group of compounds of formula I, R₂ signifies C₁-C₆-alkylsulphonyl. Also of interest are compounds of formula I, in which R₁ signifies methyl.

[0053] Particularly preferred individual compounds falling within the scope of formula I are: 4-hydroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-bicyclo[3.2.1 ]oct-3-en-2-one and 5-hydroxy-4-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-2,6,6-trimethyl-6.H.-[1,2]oxazin-3-one.

[0054] The compounds of formula I may be produced by known processes which are described, for example, in U.S. Pat. No. 5,565,410, U.S. Pat. No. 5,608,101 and EP-A-0 282 944, whereby e.g. a compound of formula II

[0055] wherein R₁, R₂, R₃ and X have the significances given under formula I and Z signifies a leaving group, preferably halogen, especially chlorine or cyano, is reacted with a compound of formula III

[0056] wherein the substituents are defined as in group Q₁, or with a compound of formula IV

[0057] wherein the substituents are defined as in group Q₂, or with a compound of formula V

[0058] wherein the substituents are defined as in group Q₃, or with a compound of formula VI

[0059] wherein the substituents are defined as in group Q₄ and correspondingly R₃₉, R₂₃, R₂₇ and R₃₃ signify hydroxy, optionally in the presence of a base. The compounds of formulae II, III, IV or V are known from U.S. Pat. No. 5,565,410, U.S. Pat. No. 5,608,101 and EP-A-0 282 944 or may be produced analogously to the processes disclosed therein.

[0060] The reactions for obtaining the compounds of formula I are advantageously carried out in aprotic inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile or propionitrile, amides such as N,N-dimethyl formamide, diethyl formamide or N-methylpyrrolidinone. The reaction temperatures are preferably in the range from −20° to +120° C. The reactions are usually slightly exothermic and can as a rule be carried out at room temperature. The reaction mixture can be heated for a brief time to boiling point to shorten the reaction time or also to initiate the reaction. The reaction times can also be shortened by addition of a few drops of a base as reaction catalyst. Particularly suitable bases are tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,5-diazabicyclo[5.4.0]undec-7-ene. Further suitable bases are also inorganic bases, typically hydrides such as sodium or calcium hydride, hydroxides such as sodium or potassium hydroxide, carbonates such as sodium and potassium carbonate, or hydrogen carbonates such as potassium and sodium hydrogen carbonate.

[0061] The compounds of formula I can be isolated in conventional manner by concentrating the reaction mixture and/or removing the solvent by evaporation and by recrystallising or triturating the solid residue in solvents in which they are not readily soluble, typically ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

[0062] The compounds of formula I or compositions containing them may be used according to this invention by all standard methods of application used in agriculture, including preemergence application, postemergence application and seed dressing, as well as by different methods and techniques such as controlled release. For controlled release, a solution of the herbicide is applied to a mineral granular carrier or to a polymerised granulate (urea/formaldehyde) and then dried. A coating can then be additionally applied (coated granules) that allows the active ingredient to be released at a controlled rate over a specific period of time.

[0063] The compounds of formula I may be used as herbicides in unmodified form, i.e. as obtained in the synthesis. Preferably they are processed in conventional manner with the auxiliary agents customarily employed in formulation technology to emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates or microcapsules. Such formulations are described, for example, in WO 97/34485 on pages 9 to 13. As with the type of agents, the methods of application such as spraying, atomising, dusting, wetting, scattering or pouring, are selected in accordance with the intended objectives and the prevailing circumstances.

[0064] The formulations, i.e. the agents, preparations, or compositions containing the compound of formula I or at least one compound of formula I and usually one or more than one liquid or solid formulation assistant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the herbicide with said formulation auxiliaries, typically solvents or solid carriers. Surface-active compounds (surfactants) may additionally be used for preparing the formulations. Examples of solvents and solid carriers are described in WO 97/34485 on page 6.

[0065] Depending on the herbicide of formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.

[0066] Examples of suitable anionic, nonionic, and cationic surfactants are listed for example in WO 97/34485 on pages 7 and 8.

[0067] Also the surfactants customary in the art of formulation and described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch” (Handbook of Surfactants), Carl Hanser Verlag, Munich/Vienna, 1981, and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-III, Chemical Publishing Co., New York, 1980-81, are suitable for manufacture of the herbicides according to the invention.

[0068] The herbicidal compositions will as a rule contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of herbicide, from 1 to 99.9% by weight, preferably from 5 to 99.8% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant. Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations. The compositions may also contain further ingredients, such as: stabilisers, e.g. where appropriate epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil, or soybean oil); anti-foaming agents, typically silicone oil; preservatives; viscosity regulators; binders; and tackifiers; as well as fertilisers or other chemical agents.

[0069] The compounds of formula I are usually applied with success to the plants or the locus thereof in concentrations of 0.001 to 4 kg/ha, preferably 0.005 to 2 kg/ha. The concentration required to achieve the desired action can be determined by experimentation. It will depend on the type of action, the development stage of the cultivated plant and of the weed, as well as on the application (locus, time, method), and as a resulty of these variables can vary over a wide range.

[0070] The compounds of formula I have excellent herbicidal and growth inhibiting properties, which make them suitable for application in crops of cultivated plants, especially in cereals, cotton, soybeans, sugar beet, sugar cane, plantations, rape, maize, and rice, and for the non-selective control of weeds. Crops will also be understood to mean those crops that have been made tolerant to herbicides or classes of herbicides by conventional breeding or genetic engineering methods. The weeds to be controlled may be monocot as well as dicot weeds, typically Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, ipomoea, Chrysanthemum, Galium, Viola, and Veronica.

[0071] The invention is illustrated by the following non-limitative Examples.

PREPARATION EXAMPLES Example P1 Preparation of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride

[0072]

[0073] A solution of 1.5 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid in 15 ml of methylene chloride produced in accordance with EP-A-0 282 944 is mixed at a temperature of 20° C. with 2 drops of DMF. Then, whilst cooling lightly, a solution of 1.0 ml (11.6 mmols) of oxalyl chloride in 2 ml of methylene chloride is added dropwise. The reaction mixture is stirred until the evolution of gas has ended. Subsequently, the solvent is distilled off. The 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride is used without further purification directly for the next step of the process.

Example P2 Preparation of 4-hydroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methylbenzoyl)-bicyclo[3.2.1]oct-3-en-2-one

[0074]

[0075] 0.8 g (5.8 mmols) of bicyclo[3.2.1]octan-2,4-dione (the preparation thereof is described for example in U.S. Pat. No. 5,608,101 and in the references cited therein) are dissolved in 15 ml of methylene chloride at 20° C. The solution is mixed with 0.97 ml of triethylamine and cooled to a temperature of 0° C. Then, a solution of 1.6 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride in 10 ml of methylene chloride is added dropwise. The reaction mixture is stirred for half an hour at a temperature of 0° C. and is subsequently diluted with methylene chloride. After washing and drying, the organic phase is concentrated by evaporation. 2.23 g of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl-ester is obtained in amorphous form. This can be used for the next step without purification.

[0076] 2.23 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoic acid-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl-ester and 1.6 ml (11.6 mmols) of triethylamine are dissolved in 20 ml of acetonitrile. 0.2 ml of acetocyanohydrin are added at a temperature of 20° C. After stirring for 20 hours, the mixture is worked up and the crude product is purified by thick-layer chromatography. 1.0 g of 4-hydroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methylbenzoyl)-bicyclo[3.2.1 ]oct-3-en-2-one is obtained in amorphous form.

Example P3 Preparation of 5-hydroxy-4-(4-methylsulphonyl-3-methoxymethyl-2-methylbenzoyl)-2,6,6-trimethyl-6.H.-[1,2]oxazin-3-one

[0077]

[0078] 0.79 g (5.04 mmols) of 2,6,6-trimethyl-2H-1,2-oxazin-3,5-dione (the preparation thereof is described for example in U.S. Pat. No. 5,565,410), 15 ml of methylene chloride and 0.97 ml of triethylamine are prepared, and at a temperature of 0° C., a solution of 1.3 g (4.7 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride in 10 ml methylene chloride is added dropwise. After stirring for 30 minutes, the solution is diluted with methylene chloride. The reaction solution is subsequently acidified with diluted hydrochloric acid, the organic phase separated, dried and concentrated. 2.0 g of 4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoic acid-2,6,6-trimethyl-5-oxo-5,6-dihydro-2.H.-[1,2]oxazin-3-yl-ester are obtained in amorphous form. The product may be further used directly without purification.

[0079] 2.0 g (5.04 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoic acid-2,6,6-trimethyl-5-oxo-5,6-dihydro-2.H.-[1,2]oxazin-3-yl-ester are dissolved in a mixture of 35 ml of acetonitrile and 10 ml of methylene chloride, then 1.4 ml (10.08 mmols) of triethylamine and 0.18 ml of acetocyanohydrin are added. After stirring for 20 hours at a temperature of 20° C. and then working up, recrystallisation is effected, and finally hydroxy-4-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-2,6,6-trimethyl-6.H.-[1,2]oxazin-3-one is obtained with a melting point of 157° C.

[0080] The substances named in the following Tables 1 to 4 may also be prepared analogously to the methods described above. In Tables 1 to 4, X denotes the following groups: X₁=CH₂OCH₃, X₂=CH₂OC₂H₅, X₃=CH₂OH, X₄=CH₂CH₂OCH₃, X₅=CH₂CH₂OC₂H₅, X₆=CH₂CH₂OCH₂CH₂OCH₃, X₇=CH₂CH₂OCH₂CH₂OC₂H₅, X₈=CH(CH₃)OC₂H₅, X₁₀=CH₂OCH₂CH═CH₂, X₁₁=CH₂OCH₂CH₂CH₃, X₁₂=CH(C₂H₅)OC₂H₅, X₁₃=C(CH₃)₂OH, X₁₄=CH₂CH₂OCH(CH₃)₂, X₁₅=CH₂SO₂CH₃, X₁₆=CH₂N(CH₃)C₂H₅, X₁₇=CH₂NHCH₃, X₁₈=CH₂OCH(CH₃)₂, X₁₉=C(CH₃)₂OCH₃, X₂₀=CH₂CH₂OH, X₂₁=CH₂OCH₂CCH, X₂₂=C(CH₃)₂OC₂H₅, X₂₃=CH(C₂H₅)OCH₃, X₂₄=CH(CH₃)OH, X₂₅=CH(OH)C₂H₅, X₂₆=CH₂SCH₃, X₂₇=CH₂N(CH₃)₂, X₂₈=CH₂CH₂N(CH₃)₂, X₂₉=CH₂OCOCH₃, X₃₀=CH₂OPh, X₃₁=CH₂CH₂OPh, X₃₂=CH₂OCH₂CH₂OCH₃, X₃₃=CH₂OCH₂CH₂OC₂H₅,

TABLE 1 Compounds of formula (Ia): (Ia)

Comp. Phys. No. V R₁₇ R₂₂ R₁ X R₂ data 1,001 CH₂ H H CH₃ X₁ SO₂CH₃ resin 1,002 CH₂ H H CH₃ X₂ SO₂CH₃ — 1,003 CH₂ H H CH₃ X₃ SO₂CH₃ — 1,004 CH₂ H H CH₃ X₄ SO₂CH₃ — 1,005 CH₂ H H CH₃ X₅ SO₂CH₃ — 1,006 CH₂ H H CH₃ X₆ SO₂CH₃ — 1,007 CH₂ H H CH₃ X₇ SO₂CH₃ — 1,008 CH₂ H H CH₃ X₈ SO₂CH₃ — 1,009 CH₂ H H CH₃ X₉ SO₂CH₃ — 1,010 CH₂ H H CH₃ X₁₀ SO₂CH₃ — 1,011 CH₂ H H CH₃ X₁₁ SO₂CH₃ — 1,012 CH₂ H H CH₃ X₁₂ SO₂CH₃ — 1,013 CH₂ H H CH₃ X₁₃ SO₂CH₃ — 1,014 CH₂ H H CH₃ X₁₄ SO₂CH₃ — 1,015 CH₂ H H CH₃ X₁₅ SO₂CH₃ — 1,016 CH₂ H H CH₃ X₁₆ SO₂CH₃ — 1,017 CH₂ H H CH₃ X₁₇ SO₂CH₃ — 1,018 CH₂ H H CH₃ X₁₈ SO₂CH₃ — 1,019 CH₂ H H CH₃ X₁₉ SO₂CH₃ — 1,020 CH₂ H H CH₃ X₂₀ SO₂CH₃ — 1,021 CH₂ H H CH₃ X₂₁ SO₂CH₃ — 1,022 CH₂ H H CH₃ X₂₂ SO₂CH₃ — 1,023 CH₂ H H CH₃ X₂₃ SO₂CH₃ — 1,024 CH₂ H H CH₃ X₂₄ SO₂CH₃ — 1,025 CH₂ H H CH₃ X₂₅ SO₂CH₃ — 1,026 CH₂ H H CH₃ X₂₆ SO₂CH₃ — 1,027 CH₂ H H CH₃ X₂₇ SO₂CH₃ — 1,028 CH₂ H H CH₃ X₂₈ SO₂CH₃ — 1,029 CH₂ H H CH₃ X₂₉ SO₂CH₃ — 1,030 CH₂ H H CH₃ X₃₀ SO₂CH₃ — 1,031 CH₂ H H CH₃ X₃₁ SO₂CH₃ — 1,032 CH₂ H H CH₃ X₃₂ SO₂CH₃ — 1,033 CH₂ H H CH₃ X₃₃ SO₂CH₃ — 1,034 CH₂ H H CH₃ X₃₄ SO₂CH₃ — 1,035 CH₂ H H CH₃ X₃₅ SO₂CH₃ — 1,036 CH₂ H H CH₃ X₃₆ SO₂CH₃ — 1,037 CH₂ H H CH₃ X₃₇ SO₂CH₃ — 1,038 CH₂ H H CH₃ X₃₈ SO₂CH₃ — 1,039 CH₂ H H CH₃ X₃₉ SO₂CH₃ — 1,040 CH₂ H H CH₃ X₄₀ SO₂CH₃ — 1,041 CH₂ H H CH₃ X₄₁ SO₂CH₃ — 1,042 CH₂ H H CH₃ X₄₂ SO₂CH₃ — 1,043 CH₂ H H CH₃ X₁ SCH₃ — 1,044 CH₂ H H CH₃ X₂ SCH₃ — 1,045 CH₂ H H CH₃ X₃ SCH₃ — 1,046 CH₂ H H CH₃ X₄ SCH₃ — 1,047 CH₂ H H CH₃ X₅ SCH₃ — 1,048 CH₂ H H CH₃ X₆ SCH₃ — 1,049 CH₂ H H CH₃ X₇ SCH₃ — 1,050 CH₂ H H CH₃ X₁₀ SCH₃ — 1,051 CH₂ H H CH₃ X₁₅ SCH₃ — 1,052 CH₂ H H CH₃ X₂₀ SCH₃ — 1,053 CH₂ H H CH₃ X₂₁ SCH₃ — 1,054 CH₂ H H CH₃ X₂₆ SCH₃ — 1,055 CH₂ H H CH₃ X₂₇ SCH₃ — 1,056 CH₂ H H CH₃ X₂₉ SCH₃ — 1,057 CH₂ H H CH₃ X₃₀ SCH₃ — 1,058 CH₃ CH₃ CH₃ CH₃ X₁ SO₂CH₃ — 1,059 CH₃ CH₃ CH₃ CH₃ X₂ SO₂CH₃ — 1,060 CH₃ CH₃ CH₃ CH₃ X₄ SO₂CH₃ — 1,061 CH₃ CH₃ CH₃ CH₃ X₁₀ SO₂CH₃ — 1,062 CH₃ CH₃ CH₃ CH₃ X₁₅ SO₂CH₃ — 1,063 CH₃ CH₃ CH₃ CH₃ X₂₁ SO₂CH₃ — 1,064 CH₃ CH₃ CH₃ CH₃ X₂₆ SO₂CH₃ — 1,065 O CH₃ CH₃ CH₃ X₁ SO₂CH₃ — 1,066 O CH₃ CH₃ CH₃ X₂ SO₂CH₃ — 1,067 O CH₃ CH₃ CH₃ X₄ SO₂CH₃ — 1,068 O CH₃ CH₃ CH₃ X₁₀ SO₂CH₃ — 1,069 O CH₃ CH₃ CH₃ X₁₅ SO₂CH₃ — 1,070 O CH₃ CH₃ CH₃ X₂₁ SO₂CH₃ — 1,071 O CH₃ CH₃ CH₃ X₂₆ SO₂CH₃ — 1,072 CH₂ H H Cl X₁ SO₂CH₃ 1,073 CH₂ H H Cl X₂ SO₂CH₃ 1,074 CH₂ H H Cl X₃ SO₂CH₃ 1,075 CH₂ H H Cl X₄ SO₂CH₃ 1,076 CH₂ H H Cl X₅ SO₂CH₃ 1,077 CH₂ H H Cl X₆ SO₂CH₃ 1,078 CH₂ H H Cl X₇ SO₂CH₃ 1,079 CH₂ H H Cl X₈ SO₂CH₃ 1,080 CH₂ H H Cl X₉ SO₂CH₃ 1,081 CH₂ H H Cl X₁₀ SO₂CH₃ 1,082 CH₂ H H Cl X₁₁ SO₂CH₃ 1,083 CH₂ H H Cl X₁₂ SO₂CH₃ 1,084 CH₂ H H Cl X₁₃ SO₂CH₃ 1,085 CH₂ H H Cl X₁₄ SO₂CH₃ 1,086 CH₂ H H Cl X₁₅ SO₂CH₃ 1,087 CH₂ H H Cl X₁₆ SO₂CH₃ 1,088 CH₂ H H Cl X₁₇ SO₂CH₃ 1,089 CH₂ H H Cl X₁₈ SO₂CH₃ 1,090 CH₂ H H Cl X₁₉ SO₂CH₃ 1,091 CH₂ H H Cl X₂₀ SO₂CH₃ 1,092 CH₂ H H Cl X₂₁ SO₂CH₃ 1,093 CH₂ H H Cl X₂₂ SO₂CH₃ 1,094 CH₂ H H Cl X₂₃ SO₂CH₃ 1,095 CH₂ H H Cl X₂₄ SO₂CH₃ 1,096 CH₂ H H Cl X₂₅ SO₂CH₃ 1,097 CH₂ H H Cl X₂₆ SO₂CH₃ 1,098 CH₂ H H Cl X₂₇ SO₂CH₃ 1,099 CH₂ H H Cl X₂₈ SO₂CH₃ 1,100 CH₂ H H Cl X₂₉ SO₂CH₃ 1,101 CH₂ H H Cl X₃₀ SO₂CH₃ 1,102 CH₂ H H Cl X₃₁ SO₂CH₃ 1,103 CH₂ H H Cl X₃₂ SO₂CH₃ 1,104 CH₂ H H Cl X₃₃ SO₂CH₃ 1,105 CH₂ H H Cl X₃₄ SO₂CH₃ 1,106 CH₂ H H Cl X₃₅ SO₂CH₃ 1,107 CH₂ H H Cl X₃₆ SO₂CH₃ 1,108 CH₂ H H Cl X₃₇ SO₂CH₃ 1,109 CH₂ H H Cl X₃₈ SO₂CH₃ 1,110 CH₂ H H Cl X₃₉ SO₂CH₃ 1,111 CH₂ H H Cl X₄₀ SO₂CH₃ 1,112 CH₂ H H Cl X₄₁ SO₂CH₃ 1,113 CH₂ H H Cl X₄₂ SO₂CH₃ 1,114 CH₂ H H CH₃ X₁ CF₃ 1,115 CH₂ H H CH₃ X₂ CF₃ 1,116 CH₂ H H CH₃ X₃ CF₃ 1,117 CH₂ H H CH₃ X₄ CF₃ 1,118 CH₂ H H CH₃ X₅ CF₃ 1,119 CH₂ H H CH₃ X₆ CF₃ 1,120 CH₂ H H CH₃ X₇ CF₃ 1,121 CH₂ H H CH₃ X₁₀ CF₃ 1,122 CH₂ H H CH₃ X₁₅ CF₃ 1,123 CH₂ H H CH₃ X₂₀ CF₃ 1,124 CH₂ H H CH₃ X₂₁ CF₃ 1,125 CH₂ H H CH₃ X₂₆ CF₃ 1,126 CH₂ H H CH₃ X₂₇ CF₃ 1,127 CH₂ H H CH₃ X₂₉ CF₃ 1,128 CH₂ H H CH₃ X₃₀ CF₃ 1,129 CH₂ H H CH₃ X₁ Br 1,130 CH₂ H H CH₃ X₂ Br 1,131 CH₂ H H CH₃ X₃ Br 1,132 CH₂ H H CH₃ X₄ Br 1,133 CH₂ H H CH₃ X₅ Br 1,134 CH₂ H H CH₃ X₆ Br 1,135 CH₂ H H CH₃ X₇ Br 1,136 CH₂ H H CH₃ X₁₀ Br 1,137 CH₂ H H CH₃ X₁₅ Br 1,138 CH₂ H H CH₃ X₂₀ Br 1,139 CH₂ H H CH₃ X₂₁ Br 1,140 CH₂ H H CH₃ X₂₆ Br 1,141 CH₂ H H CH₃ X₂₇ Br 1,142 CH₂ H H CH₃ X₂₉ Br 1,143 CH₂ H H CH₃ X₃₀ Br 1,144 CH₂ H H CH₃ X₁ CN 1,145 CH₂ H H CH₃ X₂ CN 1,146 CH₂ H H CH₃ X₃ CN 1,147 CH₂ H H CH₃ X₄ CN 1,148 CH₂ H H CH₃ X₆ CN 1,149 CH₂ H H CH₃ X₁₀ CN 1,150 CH₂ H H CH₃ X₁₅ CN 1,151 CH₂ H H CH₃ X₂₁ CN 1,152 CH₂ H H CH₃ X₂₆ CN 1,153 CH₂ H H CH₃ X₃₀ CN 1,154 CH₂ H H CF₃ X₁ SO₂CH₃ 1,155 CH₂ H H CF₃ X₂ SO₂CH₃ 1,156 CH₂ H H CF₃ X₃ SO₂CH₃ 1,157 CH₂ H H CF₃ X₄ SO₂CH₃ 1,158 CH₂ H H CF₃ X₆ SO₂CH₃ 1,159 CH₂ H H CF₃ X₁₀ SO₂CH₃ 1,160 CH₂ H H CF₃ X₁₅ SO₂CH₃ 1,161 CH₂ H H CF₃ X₂₁ SO₂CH₃ 1,162 CH₂ H H CF₃ X₂₆ SO₂CH₃ 1,163 CH₂ H H CF₃ X₃₀ SO₂CH₃ 1,164 CH₃ CH₃ CH₃ CF₃ X₁ SO₂CH₃ 1,165 CH₃ CH₃ CH₃ CF₃ X₂ SO₂CH₃ 1,166 CH₃ CH₃ CH₃ CF₃ X₄ SO₂CH₃ 1,167 CH₃ CH₃ CH₃ CF₃ X₁₀ SO₂CH₃ 1,168 CH₃ CH₃ CH₃ CF₃ X₁₅ SO₂CH₃ 1,169 CH₃ CH₃ CH₃ CF₃ X₂₁ SO₂CH₃ 1,170 CH₃ CH₃ CH₃ CF₃ X₂₆ SO₂CH₃ 1,171 CH₂ H H SO₂CH₃ X₁ CF₃ 1,172 CH₂ H H SO₂CH₃ X₂ CF₃ 1,173 CH₂ H H SO₂CH₃ X₃ CF₃ 1,174 CH₂ H H SO₂CH₃ X₄ CF₃ 1,175 CH₂ H H SO₂CH₃ X₆ CF₃ 1,176 CH₂ H H SO₂CH₃ X₁₀ CF₃ 1,177 CH₂ H H SO₂CH₃ X₁₅ CF₃ 1,178 CH₂ H H SO₂CH₃ X₂₁ CF₃ 1,179 CH₂ H H SO₂CH₃ X₂₆ CF₃ 1,180 CH₂ H H SO₂CH₃ X₃₀ CF₃ 1,181 CH₂ H H CH₃ X₁ Cl 1,182 CH₂ H H CH₃ X₂ Cl 1,183 CH₂ H H CH₃ X₃ Cl 1,184 CH₂ H H CH₃ X₄ Cl 1,185 CH₂ H H CH₃ X₆ Cl 1,186 CH₂ H H CH₃ X₁₀ Cl 1,187 CH₂ H H CH₃ X₁₅ Cl 1,188 CH₂ H H CH₃ X₂₁ Cl 1,189 CH₂ H H CH₃ X₂₆ Cl 1,190 CH₂ H H CH₃ X₃₀ Cl 1,191 CH₂ H H NO₂ X₁ SO₂CH₃ 1,192 CH₂ H H NO₂ X₂ SO₂CH₃ 1,193 CH₂ H H NO₂ X₄ SO₂CH₃ 1,194 CH₂ H H NO₂ X₁₀ SO₂CH₃ 1,195 CH₂ H H NO₂ X₁₅ SO₂CH₃ 1,196 CH₂ H H NO₂ X₂₁ SO₂CH₃ 1,197 CH₂ H H NO₂ X₂₆ SO₂CH₃

[0081] TABLE 2 Compounds of formula (Ib): (Ib)

Comp. m.p. No. R₂₄ R₂₅ R₂₆ R₁ X R₂ (° C.) 2,001 CH₃ CH₃ CH₃ CH₃ X₁ SO₂CH₃ 157° C. 2,002 CH₃ CH₃ CH₃ CH₃ X₂ SO₂CH₃ — 2,003 CH₃ CH₃ CH₃ CH₃ X₃ SO₂CH₃ — 2,004 CH₃ CH₃ CH₃ CH₃ X₄ SO₂CH₃ — 2,005 CH₃ CH₃ CH₃ CH₃ X₅ SO₂CH₃ — 2,006 CH₃ CH₃ CH₃ CH₃ X₆ SO₂CH₃ — 2,007 CH₃ CH₃ CH₃ CH₃ X₇ SO₂CH₃ — 2,008 CH₃ CH₃ CH₃ CH₃ X₈ SO₂CH₃ — 2,009 CH₃ CH₃ CH₃ CH₃ X₉ SO₂CH₃ — 2,010 CH₃ CH₃ CH₃ CH₃ X₁₀ SO₂CH₃ — 2,011 CH₃ CH₃ CH₃ CH₃ X₁₁ SO₂CH₃ — 2,012 CH₃ CH₃ CH₃ CH₃ X₁₂ SO₂CH₃ — 2,013 CH₃ CH₃ CH₃ CH₃ X₁₃ SO₂CH₃ — 2,014 CH₃ CH₃ CH₃ CH₃ X₁₄ SO₂CH₃ — 2,015 CH₃ CH₃ CH₃ CH₃ X₁₅ SO₂CH₃ — 2,016 CH₃ CH₃ CH₃ CH₃ X₁₆ SO₂CH₃ — 2,017 CH₃ CH₃ CH₃ CH₃ X₁₇ SO₂CH₃ — 2,018 CH₃ CH₃ CH₃ CH₃ X₁₈ SO₂CH₃ — 2,019 CH₃ CH₃ CH₃ CH₃ X₁₉ SO₂CH₃ — 2,020 CH₃ CH₃ CH₃ CH₃ X₂₀ SO₂CH₃ — 2,021 CH₃ CH₃ CH₃ CH₃ X₂₁ SO₂CH₃ — 2,022 CH₃ CH₃ CH₃ CH₃ X₂₂ SO₂CH₃ — 2,023 CH₃ CH₃ CH₃ CH₃ X₂₃ SO₂CH₃ — 2,024 CH₃ CH₃ CH₃ CH₃ X₂₄ SO₂CH₃ — 2,025 CH₃ CH₃ CH₃ CH₃ X₂₅ SO₂CH₃ — 2,026 CH₃ CH₃ CH₃ CH₃ X₂₆ SO₂CH₃ — 2,027 CH₃ CH₃ CH₃ CH₃ X₂₇ SO₂CH₃ — 2,028 CH₃ CH₃ CH₃ CH₃ X₂₈ SO₂CH₃ — 2,029 CH₃ CH₃ CH₃ CH₃ X₂₉ SO₂CH₃ — 2,030 CH₃ CH₃ CH₃ CH₃ X₃₀ SO₂CH₃ — 2,031 CH₃ CH₃ CH₃ CH₃ X₃₁ SO₂CH₃ — 2,032 CH₃ CH₃ CH₃ CH₃ X₃₂ SO₂CH₃ — 2,033 CH₃ CH₃ CH₃ CH₃ X₃₃ SO₂CH₃ — 2,034 CH₃ CH₃ CH₃ CH₃ X₃₄ SO₂CH₃ — 2,035 CH₃ CH₃ CH₃ CH₃ X₃₅ SO₂CH₃ — 2,036 CH₃ CH₃ CH₃ CH₃ X₃₆ SO₂CH₃ — 2,037 CH₃ CH₃ CH₃ CH₃ X₃₇ SO₂CH₃ — 2,038 CH₃ CH₃ CH₃ CH₃ X₃₈ SO₂CH₃ — 2,039 CH₃ CH₃ CH₃ CH₃ X₃₉ SO₂CH₃ — 2,040 CH₃ CH₃ CH₃ CH₃ X₄₀ SO₂CH₃ — 2,041 CH₃ CH₃ CH₃ CH₃ X₄₁ SO₂CH₃ — 2,042 CH₃ CH₃ CH₃ CH₃ X₄₂ SO₂CH₃ — 2,043 CH₃ CH₃ CH₃ Cl X₁ SO₂CH₃ — 2,044 CH₃ CH₃ CH₃ Cl X₂ SO₂CH₃ — 2,045 CH₃ CH₃ CH₃ Cl X₃ SO₂CH₃ — 2,046 CH₃ CH₃ CH₃ Cl X₄ SO₂CH₃ — 2,047 CH₃ CH₃ CH₃ Cl X₅ SO₂CH₃ — 2,048 CH₃ CH₃ CH₃ Cl X₆ SO₂CH₃ — 2,049 CH₃ CH₃ CH₃ Cl X₇ SO₂CH₃ — 2,050 CH₃ CH₃ CH₃ Cl X₁₀ SO₂CH₃ — 2,051 CH₃ CH₃ CH₃ Cl X₁₅ SO₂CH₃ — 2,052 CH₃ CH₃ CH₃ Cl X₂₀ SO₂CH₃ — 2,053 CH₃ CH₃ CH₃ Cl X₂₁ SO₂CH₃ — 2,054 CH₃ CH₃ CH₃ Cl X₂₆ SO₂CH₃ — 2,055 CH₃ CH₃ CH₃ Cl X₂₇ SO₂CH₃ — 2,056 CH₃ CH₃ CH₃ Cl X₂₉ SO₂CH₃ — 2,057 CH₃ CH₃ CH₃ Cl X₃₀ SO₂CH₃ — 2,058 CH₃ CH₃ CH₃ CH₃ X₁ SCH₃ — 2,059 CH₃ CH₃ CH₃ CH₃ X₂ SCH₃ — 2,060 CH₃ CH₃ CH₃ CH₃ X₃ SCH₃ — 2,061 CH₃ CH₃ CH₃ CH₃ X₄ SCH₃ — 2,062 CH₃ CH₃ CH₃ CH₃ X₅ SCH₃ — 2,063 CH₃ CH₃ CH₃ CH₃ X₆ SCH₃ — 2,064 CH₃ CH₃ CH₃ CH₃ X₇ SCH₃ — 2,065 CH₃ CH₃ CH₃ CH₃ X₁₀ SCH₃ — 2,066 CH₃ CH₃ CH₃ CH₃ X₁₅ SCH₃ — 2,067 CH₃ CH₃ CH₃ CH₃ X₂₀ SCH₃ — 2,068 CH₃ CH₃ CH₃ CH₃ X₂₁ SCH₃ — 2,069 CH₃ CH₃ CH₃ CH₃ X₂₆ SCH₃ — 2,070 CH₃ CH₃ CH₃ CH₃ X₂₇ SCH₃ — 2,071 CH₃ CH₃ CH₃ CH₃ X₂₉ SCH₃ — 2,072 CH₃ CH₃ CH₃ CH₃ X₃₀ SCH₃ — 2,073 H H C₂H₅ CH₃ X₁ SO₂CH₃ — 2,074 H H C₂H₅ CH₃ X₂ SO₂CH₃ — 2,075 H H C₂H₅ CH₃ X₄ SO₂CH₃ — 2,076 H H C₂H₅ CH₃ X₁₀ SO₂CH₃ — 2,077 H H C₂H₅ CH₃ X₁₅ SO₂CH₃ — 2,078 H H C₂H₅ CH₃ X₂₁ SO₂CH₃ — 2,079 H H C₂H₅ CH₃ X₂₆ SO₂CH₃ — 2,080 H H C₃H₇ CH₃ X₁ SO₂CH₃ — 2,081 H H C₃H₇ CH₃ X₂ SO₂CH₃ — 2,082 H H C₃H₇ CH₃ X₄ SO₂CH₃ — 2,083 H H C₃H₇ CH₃ X₁₀ SO₂CH₃ — 2,084 H H C₃H₇ CH₃ X₁₅ SO₂CH₃ — 2,085 H H C₃H₇ CH₃ X₂₁ SO₂CH₃ — 2,086 H H C₃H₇ CH₃ X₂₆ SO₂CH₃ — 2,087 CH₃ CH₃ CH₃ Cl X₁ SCH₃ — 2,088 CH₃ CH₃ CH₃ Cl X₂ SCH₃ — 2,089 CH₃ CH₃ CH₃ Cl X₄ SCH₃ — 2,090 CH₃ CH₃ CH₃ Cl X₂₆ SCH₃ — 2,091 CH₃ CH₃ CH₃ CH₃ X₁ CF₃ — 2,092 CH₃ CH₃ CH₃ CH₃ X₂ CF₃ — 2,093 CH₃ CH₃ CH₃ CH₃ X₃ CF₃ — 2,094 CH₃ CH₃ CH₃ CH₃ X₄ CF₃ — 2,095 CH₃ CH₃ CH₃ CH₃ X₆ CF₃ — 2,096 CH₃ CH₃ CH₃ CH₃ X₁₀ CF₃ — 2,097 CH₃ CH₃ CH₃ CH₃ X₁₅ CF₃ — 2,098 CH₃ CH₃ CH₃ CH₃ X₂₁ CF₃ — 2,099 CH₃ CH₃ CH₃ CH₃ X₂₆ CF₃ — 2,100 CH₃ CH₃ CH₃ CH₃ X₃₀ CF₃ — 2,101 CH₃ CH₃ CH₃ SO₂CH₃ X₁ CF₃ — 2,102 CH₃ CH₃ CH₃ SO₂CH₃ X₂ CF₃ — 2,103 CH₃ CH₃ CH₃ SO₂CH₃ X₄ CF₃ — 2,104 CH₃ CH₃ CH₃ SO₂CH₃ X₂₆ CF₃ — 2,105 CH₃ CH₃ CH₃ NO₂ X₁ CF₃ — 2,106 CH₃ CH₃ CH₃ NO₂ X₂ CF₃ — 2,107 CH₃ CH₃ CH₃ NO₂ X₄ CF₃ — 2,108 CH₃ CH₃ CH₃ NO₂ X₂₆ CF₃ — 2,109 CH₃ CH₃ CH₃ NO₂ X₁ SO₂CH₃ — 2,110 CH₃ CH₃ CH₃ NO₂ X₂ SO₂CH₃ — 2,111 CH₃ CH₃ CH₃ NO₂ X₄ SO₂CH₃ — 2,112 CH₃ CH₃ CH₃ NO₂ X₂₆ SO₂CH₃ — 2,113 CH₃ CH₃ CH₃ Br X₁ SO₂CH₃ — 2,114 CH₃ CH₃ CH₃ Br X₂ SO₂CH₃ — 2,115 CH₃ CH₃ CH₃ Br X₄ SO₂CH₃ — 2,116 CH₃ CH₃ CH₃ Br X₂₆ SO₂CH₃ —

[0082] TABLE 3 Compounds of formula (Ic): (Ic)

Comp. Phys. No. R₂₈ R₂₉ R₃₀ R₁ X R₂ data 3,001 CH₃ CH₃ CH₃ CH₃ X₁ SO₂CH₃ — 3,002 CH₃ CH₃ CH₃ CH₃ X₂ SO₂CH₃ — 3,003 CH₃ CH₃ CH₃ CH₃ X₃ SO₂CH₃ — 3,004 CH₃ CH₃ CH₃ CH₃ X₄ SO₂CH₃ — 3,005 CH₃ CH₃ CH₃ CH₃ X₅ SO₂CH₃ — 3,006 CH₃ CH₃ CH₃ CH₃ X₆ SO₂CH₃ — 3,007 CH₃ CH₃ CH₃ CH₃ X₇ SO₂CH₃ — 3,008 CH₃ CH₃ CH₃ CH₃ X₈ SO₂CH₃ — 3,009 CH₃ CH₃ CH₃ CH₃ X₉ SO₂CH₃ — 3,010 CH₃ CH₃ CH₃ CH₃ X₁₀ SO₂CH₃ — 3,011 CH₃ CH₃ CH₃ CH₃ X₁₁ SO₂CH₃ — 3,012 CH₃ CH₃ CH₃ CH₃ X₁₂ SO₂CH₃ — 3,013 CH₃ CH₃ CH₃ CH₃ X₁₃ SO₂CH₃ — 3,014 CH₃ CH₃ CH₃ CH₃ X₁₄ SO₂CH₃ — 3,015 CH₃ CH₃ CH₃ CH₃ X₁₅ SO₂CH₃ — 3,016 CH₃ CH₃ CH₃ CH₃ X₁₆ SO₂CH₃ — 3,017 CH₃ CH₃ CH₃ CH₃ X₁₇ SO₂CH₃ — 3,018 CH₃ CH₃ CH₃ CH₃ X₁₈ SO₂CH₃ — 3,019 CH₃ CH₃ CH₃ CH₃ X₁₉ SO₂CH₃ — 3,020 CH₃ CH₃ CH₃ CH₃ X₂₀ SO₂CH₃ — 3,021 CH₃ CH₃ CH₃ CH₃ X₂₁ SO₂CH₃ — 3,022 CH₃ CH₃ CH₃ CH₃ X₂₂ SO₂CH₃ — 3,023 CH₃ CH₃ CH₃ CH₃ X₂₃ SO₂CH₃ — 3,024 CH₃ CH₃ CH₃ CH₃ X₂₄ SO₂CH₃ — 3,025 CH₃ CH₃ CH₃ CH₃ X₂₅ SO₂CH₃ — 3,026 CH₃ CH₃ CH₃ CH₃ X₂₆ SO₂CH₃ — 3,027 CH₃ CH₃ CH₃ CH₃ X₂₇ SO₂CH₃ — 3,028 CH₃ CH₃ CH₃ CH₃ X₂₈ SO₂CH₃ — 3,029 CH₃ CH₃ CH₃ CH₃ X₂₉ SO₂CH₃ — 3,030 CH₃ CH₃ CH₃ CH₃ X₃₀ SO₂CH₃ — 3,031 CH₃ CH₃ CH₃ CH₃ X₃₁ SO₂CH₃ — 3,032 CH₃ CH₃ CH₃ CH₃ X₃₂ SO₂CH₃ — 3,033 CH₃ CH₃ CH₃ CH₃ X₃₃ SO₂CH₃ — 3,034 CH₃ CH₃ CH₃ CH₃ X₃₄ SO₂CH₃ — 3,035 CH₃ CH₃ CH₃ CH₃ X₃₅ SO₂CH₃ — 3,036 CH₃ CH₃ CH₃ CH₃ X₃₆ SO₂CH₃ — 3,037 CH₃ CH₃ CH₃ CH₃ X₃₇ SO₂CH₃ — 3,038 CH₃ CH₃ CH₃ CH₃ X₃₈ SO₂CH₃ — 3,039 CH₃ CH₃ CH₃ CH₃ X₃₉ SO₂CH₃ — 3,040 CH₃ CH₃ CH₃ CH₃ X₄₀ SO₂CH₃ — 3,041 CH₃ CH₃ CH₃ CH₃ X₄₁ SO₂CH₃ — 3,042 CH₃ CH₃ CH₃ CH₃ X₄₂ SO₂CH₃ — 3,043 CH₃ CH₃ CH₃ CH₃ X₁ SCH₃ — 3,044 CH₃ CH₃ CH₃ CH₃ X₂ SCH₃ — 3,045 CH₃ CH₃ CH₃ CH₃ X₃ SCH₃ — 3,046 CH₃ CH₃ CH₃ CH₃ X₄ SCH₃ — 3,047 CH₃ CH₃ CH₃ CH₃ X₅ SCH₃ — 3,048 CH₃ CH₃ CH₃ CH₃ X₆ SCH₃ — 3,049 CH₃ CH₃ CH₃ CH₃ X₇ SCH₃ — 3,050 CH₃ CH₃ CH₃ CH₃ X₁₀ SCH₃ — 3,051 CH₃ CH₃ CH₃ CH₃ X₁₅ SCH₃ — 3,052 CH₃ CH₃ CH₃ CH₃ X₂₀ SCH₃ — 3,053 CH₃ CH₃ CH₃ CH₃ X₂₁ SCH₃ — 3,054 CH₃ CH₃ CH₃ CH₃ X₂₆ SCH₃ — 3,055 CH₃ CH₃ CH₃ CH₃ X₂₇ SCH₃ — 3,056 CH₃ CH₃ CH₃ CH₃ X₂₉ SCH₃ — 3,057 CH₃ CH₃ CH₃ CH₃ X₃₀ SCH₃ — 3,058 CH₃ CH₃ CH₃ Cl X₁ SO₂CH₃ — 3,059 CH₃ CH₃ CH₃ Cl X₂ SO₂CH₃ — 3,060 CH₃ CH₃ CH₃ Cl X₃ SO₂CH₃ — 3,061 CH₃ CH₃ CH₃ Cl X₄ SO₂CH₃ — 3,062 CH₃ CH₃ CH₃ Cl X₅ SO₂CH₃ — 3,063 CH₃ CH₃ CH₃ Cl X₆ SO₂CH₃ — 3,064 CH₃ CH₃ CH₃ Cl X₇ SO₂CH₃ — 3,065 CH₃ CH₃ CH₃ Cl X₈ SO₂CH₃ — 3,066 CH₃ CH₃ CH₃ Cl X₉ SO₂CH₃ — 3,067 CH₃ CH₃ CH₃ Cl X₁₀ SO₂CH₃ — 3,068 CH₃ CH₃ CH₃ Cl X₁₁ SO₂CH₃ — 3,069 CH₃ CH₃ CH₃ Cl X₁₂ SO₂CH₃ — 3,070 CH₃ CH₃ CH₃ Cl X₁₃ SO₂CH₃ — 3,071 CH₃ CH₃ CH₃ Cl X₁₄ SO₂CH₃ — 3,072 CH₃ CH₃ CH₃ Cl X₁₅ SO₂CH₃ — 3,073 CH₃ CH₃ CH₃ Cl X₁₆ SO₂CH₃ — 3,074 CH₃ CH₃ CH₃ Cl X₁₇ SO₂CH₃ — 3,075 CH₃ CH₃ CH₃ Cl X₁₈ SO₂CH₃ — 3,076 CH₃ CH₃ CH₃ Cl X₁₉ SO₂CH₃ — 3,077 CH₃ CH₃ CH₃ Cl X₂₀ SO₂CH₃ — 3,078 CH₃ CH₃ CH₃ Cl X₂₁ SO₂CH₃ — 3,079 CH₃ CH₃ CH₃ Cl X₂₂ SO₂CH₃ — 3,080 CH₃ CH₃ CH₃ Cl X₂₃ SO₂CH₃ — 3,081 CH₃ CH₃ CH₃ Cl X₂₄ SO₂CH₃ — 3,082 CH₃ CH₃ CH₃ Cl X₂₅ SO₂CH₃ — 3,083 CH₃ CH₃ CH₃ Cl X₂₆ SO₂CH₃ — 3,084 CH₃ CH₃ CH₃ Cl X₂₇ SO₂CH₃ — 3,085 CH₃ CH₃ CH₃ Cl X₂₈ SO₂CH₃ — 3,086 CH₃ CH₃ CH₃ Cl X₂₉ SO₂CH₃ — 3,087 CH₃ CH₃ CH₃ Cl X₃₀ SO₂CH₃ — 3,088 CH₃ CH₃ CH₃ Cl X₃₁ SO₂CH₃ — 3,089 CH₃ CH₃ CH₃ Cl X₃₂ SO₂CH₃ — 3,090 CH₃ CH₃ CH₃ Cl X₃₃ SO₂CH₃ — 3,091 CH₃ CH₃ CH₃ Cl X₃₄ SO₂CH₃ — 3,092 CH₃ CH₃ CH₃ Cl X₃₅ SO₂CH₃ — 3,093 CH₃ CH₃ CH₃ Cl X₃₆ SO₂CH₃ — 3,094 CH₃ CH₃ CH₃ Cl X₃₇ SO₂CH₃ — 3,095 CH₃ CH₃ CH₃ Cl X₃₈ SO₂CH₃ — 3,096 CH₃ CH₃ CH₃ Cl X₃₉ SO₂CH₃ — 3,097 CH₃ CH₃ CH₃ Cl X₄₀ SO₂CH₃ — 3,098 CH₃ CH₃ CH₃ Cl X₄₁ SO₂CH₃ — 3,099 CH₃ CH₃ CH₃ Cl X₄₂ SO₂CH₃ — 3,100 CH₃ CH₃ CH₃ CH₃ X₁ CF₃ — 3,101 CH₃ CH₃ CH₃ CH₃ X₂ CF₃ — 3,102 CH₃ CH₃ CH₃ CH₃ X₃ CF₃ — 3,103 CH₃ CH₃ CH₃ CH₃ X₄ CF₃ — 3,104 CH₃ CH₃ CH₃ CH₃ X₆ CF₃ — 3,105 CH₃ CH₃ CH₃ CH₃ X₁₀ CF₃ — 3,106 CH₃ CH₃ CH₃ CH₃ X₁₅ CF₃ — 3,107 CH₃ CH₃ CH₃ CH₃ X₂₁ CF₃ — 3,108 CH₃ CH₃ CH₃ CH₃ X₂₆ CF₃ — 3,109 CH₃ CH₃ CH₃ CH₃ X₃₀ CF₃ — 3,110 CH₃ CH₃ CH₃ NO₂ X₁ SO₂CH₃ — 3,111 CH₃ CH₃ CH₃ NO₂ X₂ SO₂CH₃ — 3,112 CH₃ CH₃ CH₃ NO₂ X₄ SO₂CH₃ — 3,113 CH₃ CH₃ CH₃ NO₂ X₂₆ SO₂CH₃ — 3,114 CH₃ CH₃ CH₃ NO₂ X₁ CF₃ — 3,115 CH₃ CH₃ CH₃ NO₂ X₂ CF₃ — 3,116 CH₃ CH₃ CH₃ NO₂ X₄ CF₃ — 3,117 CH₃ CH₃ CH₃ NO₂ X₂₆ CF₃ — 3,118 CH₃ C₂H₅ CH₃ CH₃ X₁ SO₂CH₃ — 3,119 CH₃ C₂H₅ CH₃ CH₃ X₂ SO₂CH₃ — 3,120 CH₃ C₂H₅ CH₃ CH₃ X₃ SO₂CH₃ — 3,121 CH₃ C₂H₅ CH₃ CH₃ X₄ SO₂CH₃ — 3,122 CH₃ C₂H₅ CH₃ CH₃ X₆ SO₂CH₃ — 3,123 CH₃ C₂H₅ CH₃ CH₃ X₁₀ SO₂CH₃ — 3,124 CH₃ C₂H₅ CH₃ CH₃ X₁₅ SO₂CH₃ — 3,125 CH₃ C₂H₅ CH₃ CH₃ X₂₁ SO₂CH₃ — 3,126 CH₃ C₂H₅ CH₃ CH₃ X₂₆ SO₂CH₃ — 3,127 CH₃ C₂H₅ CH₃ CH₃ X₃₀ SO₂CH₃ — 3,128 C₂H₅ C₂H₅ CH₃ CH₃ X₁ SO₂CH₃ — 3,129 C₂H₅ C₂H₅ CH₃ CH₃ X₂ SO₂CH₃ — 3,130 C₂H₅ C₂H₅ CH₃ CH₃ X₄ SO₂CH₃ — 3,131 C₂H₅ C₂H₅ CH₃ CH₃ X₁₀ SO₂CH₃ — 3,132 C₂H₅ C₂H₅ CH₃ CH₃ X₁₅ SO₂CH₃ — 3,133 C₂H₅ C₂H₅ CH₃ CH₃ X₂₁ SO₂CH₃ — 3,134 C₂H₅ C₂H₅ CH₃ CH₃ X₂₆ SO₂CH₃ — 3,135 CH₃ CH₃ CH₃ Cl X₁ SCH₃ — 3,136 CH₃ CH₃ CH₃ Cl X₂ SCH₃ — 3,137 CH₃ CH₃ CH₃ Cl X₃ SCH₃ — 3,138 CH₃ CH₃ CH₃ Cl X₄ SCH₃ — 3,139 CH₃ CH₃ CH₃ Cl X₅ SCH₃ — 3,140 CH₃ CH₃ CH₃ Cl X₆ SCH₃ — 3,141 CH₃ CH₃ CH₃ Cl X₇ SCH₃ — 3,142 CH₃ CH₃ CH₃ Cl X₁₀ SCH₃ — 3,143 CH₃ CH₃ CH₃ Cl X₁₅ SCH₃ — 3,144 CH₃ CH₃ CH₃ Cl X₂₀ SCH₃ — 3,145 CH₃ CH₃ CH₃ Cl X₂₁ SCH₃ — 3,146 CH₃ CH₃ CH₃ Cl X₂₆ SCH₃ — 3,147 CH₃ CH₃ CH₃ Cl X₂₇ SCH₃ — 3,148 CH₃ CH₃ CH₃ Cl X₂₉ SCH₃ — 3,149 CH₃ CH₃ CH₃ Cl X₃₀ SCH₃ —

[0083] TABLE 4 Compounds of formula (Id): (Id)

Comp. Phys. No. R₃₆ R₃₇ W R₁ X R₂ data 4,001 CH₃ CH₃ O CH₃ X₁ SO₂CH₃ — 4,002 CH₃ CH₃ O CH₃ X₂ SO₂CH₃ — 4,003 CH₃ CH₃ O CH₃ X₃ SO₂CH₃ — 4,004 CH₃ CH₃ O CH₃ X₄ SO₂CH₃ — 4,005 CH₃ CH₃ O CH₃ X₅ SO₂CH₃ — 4,006 CH₃ CH₃ O CH₃ X₆ SO₂CH₃ — 4,007 CH₃ CH₃ O CH₃ X₇ SO₂CH₃ — 4,008 CH₃ CH₃ O CH₃ X₈ SO₂CH₃ — 4,009 CH₃ CH₃ O CH₃ X₉ SO₂CH₃ — 4,010 CH₃ CH₃ O CH₃ X₁₀ SO₂CH₃ — 4,011 CH₃ CH₃ O CH₃ X₁₁ SO₂CH₃ — 4,012 CH₃ CH₃ O CH₃ X₁₂ SO₂CH₃ — 4,013 CH₃ CH₃ O CH₃ X₁₃ SO₂CH₃ — 4,014 CH₃ CH₃ O CH₃ X₁₄ SO₂CH₃ — 4,015 CH₃ CH₃ O CH₃ X₁₅ SO₂CH₃ — 4,016 CH₃ CH₃ O CH₃ X₁₆ SO₂CH₃ — 4,017 CH₃ CH₃ O CH₃ X₁₇ SO₂CH₃ — 4,018 CH₃ CH₃ O CH₃ X₁₈ SO₂CH₃ — 4,019 CH₃ CH₃ O CH₃ X₁₉ SO₂CH₃ — 4,020 CH₃ CH₃ O CH₃ X₂₀ SO₂CH₃ — 4,021 CH₃ CH₃ O CH₃ X₂₁ SO₂CH₃ — 4,022 CH₃ CH₃ O CH₃ X₂₂ SO₂CH₃ — 4,023 CH₃ CH₃ O CH₃ X₂₃ SO₂CH₃ — 4,024 CH₃ CH₃ O CH₃ X₂₄ SO₂CH₃ — 4,025 CH₃ CH₃ O CH₃ X₂₅ SO₂CH₃ — 4,026 CH₃ CH₃ O CH₃ X₂₆ SO₂CH₃ — 4,027 CH₃ CH₃ O CH₃ X₂₇ SO₂CH₃ — 4,028 CH₃ CH₃ O CH₃ X₂₈ SO₂CH₃ — 4,029 CH₃ CH₃ O CH₃ X₂₉ SO₂CH₃ — 4,030 CH₃ CH₃ O CH₃ X₃₀ SO₂CH₃ — 4,031 CH₃ CH₃ O CH₃ X₃₁ SO₂CH₃ — 4,032 CH₃ CH₃ O CH₃ X₃₂ SO₂CH₃ — 4,033 CH₃ CH₃ O CH₃ X₃₃ SO₂CH₃ — 4,034 CH₃ CH₃ O CH₃ X₃₄ SO₂CH₃ — 4,035 CH₃ CH₃ O CH₃ X₃₅ SO₂CH₃ — 4,036 CH₃ CH₃ O CH₃ X₃₆ SO₂CH₃ — 4,037 CH₃ CH₃ O CH₃ X₃₇ SO₂CH₃ — 4,038 CH₃ CH₃ O CH₃ X₃₈ SO₂CH₃ — 4,039 CH₃ CH₃ O CH₃ X₃₉ SO₂CH₃ — 4,040 CH₃ CH₃ O CH₃ X₄₀ SO₂CH₃ — 4,041 CH₃ CH₃ O CH₃ X₄₁ SO₂CH₃ — 4,042 CH₃ CH₃ O CH₃ X₄₂ SO₂CH₃ — 4,043 CH₃ CH₃ O CH₃ X₁ SCH₃ — 4,044 CH₃ CH₃ O CH₃ X₂ SCH₃ — 4,045 CH₃ CH₃ O CH₃ X₃ SCH₃ — 4,046 CH₃ CH₃ O CH₃ X₄ SCH₃ — 4,047 CH₃ CH₃ O CH₃ X₅ SCH₃ — 4,048 CH₃ CH₃ O CH₃ X₆ SCH₃ — 4,049 CH₃ CH₃ O CH₃ X₇ SCH₃ — 4,050 CH₃ CH₃ O CH₃ X₁₀ SCH₃ — 4,051 CH₃ CH₃ O CH₃ X₁₅ SCH₃ — 4,052 CH₃ CH₃ O CH₃ X₂₀ SCH₃ — 4,053 CH₃ CH₃ O CH₃ X₂₁ SCH₃ — 4,054 CH₃ CH₃ O CH₃ X₂₆ SCH₃ — 4,055 CH₃ CH₃ O CH₃ X₂₇ SCH₃ — 4,056 CH₃ CH₃ O CH₃ X₂₉ SCH₃ — 4,057 CH₃ CH₃ O CH₃ X₃₀ SCH₃ — 4,058 CH₃ CH₃ O Cl X₁ SO₂CH₃ — 4,059 CH₃ CH₃ O Cl X₂ SO₂CH₃ — 4,060 CH₃ CH₃ O Cl X₃ SO₂CH₃ — 4,061 CH₃ CH₃ O Cl X₄ SO₂CH₃ — 4,062 CH₃ CH₃ O Cl X₅ SO₂CH₃ — 4,063 CH₃ CH₃ O Cl X₆ SO₂CH₃ — 4,064 CH₃ CH₃ O Cl X₇ SO₂CH₃ — 4,065 CH₃ CH₃ O Cl X₈ SO₂CH₃ — 4,066 CH₃ CH₃ O Cl X₉ SO₂CH₃ — 4,067 CH₃ CH₃ O Cl X₁₀ SO₂CH₃ — 4,068 CH₃ CH₃ O Cl X₁₁ SO₂CH₃ — 4,069 CH₃ CH₃ O Cl X₁₂ SO₂CH₃ — 4,070 CH₃ CH₃ O Cl X₁₃ SO₂CH₃ — 4,071 CH₃ CH₃ O Cl X₁₄ SO₂CH₃ — 4,072 CH₃ CH₃ O Cl X₁₅ SO₂CH₃ — 4,073 CH₃ CH₃ O Cl X₁₆ SO₂CH₃ — 4,074 CH₃ CH₃ O Cl X₁₇ SO₂CH₃ — 4,075 CH₃ CH₃ O Cl X₁₈ SO₂CH₃ — 4,076 CH₃ CH₃ O Cl X₁₉ SO₂CH₃ — 4,077 CH₃ CH₃ O Cl X₂₀ SO₂CH₃ — 4,078 CH₃ CH₃ O Cl X₂₁ SO₂CH₃ — 4,079 CH₃ CH₃ O Cl X₂₂ SO₂CH₃ — 4,080 CH₃ CH₃ O Cl X₂₃ SO₂CH₃ — 4,081 CH₃ CH₃ O Cl X₂₄ SO₂CH₃ — 4,082 CH₃ CH₃ O Cl X₂₅ SO₂CH₃ — 4,083 CH₃ CH₃ O Cl X₂₆ SO₂CH₃ — 4,084 CH₃ CH₃ O Cl X₂₇ SO₂CH₃ — 4,085 CH₃ CH₃ O Cl X₂₈ SO₂CH₃ — 4,086 CH₃ CH₃ O Cl X₂₉ SO₂CH₃ — 4,087 CH₃ CH₃ O Cl X₃₀ SO₂CH₃ — 4,088 CH₃ CH₃ O Cl X₃₁ SO₂CH₃ — 4,089 CH₃ CH₃ O Cl X₃₂ SO₂CH₃ — 4,090 CH₃ CH₃ O Cl X₃₃ SO₂CH₃ — 4,091 CH₃ CH₃ O Cl X₃₄ SO₂CH₃ — 4,092 CH₃ CH₃ O Cl X₃₅ SO₂CH₃ — 4,093 CH₃ CH₃ O Cl X₃₆ SO₂CH₃ — 4,094 CH₃ CH₃ O Cl X₃₇ SO₂CH₃ — 4,095 CH₃ CH₃ O Cl X₃₈ SO₂CH₃ — 4,096 CH₃ CH₃ O Cl X₃₉ SO₂CH₃ — 4,097 CH₃ CH₃ O Cl X₄₀ SO₂CH₃ — 4,098 CH₃ CH₃ O Cl X₄₁ SO₂CH₃ — 4,099 CH₃ CH₃ O Cl X₄₂ SO₂CH₃ — 4,100 CH₃ CH₃ O CH₃ X₁ CF₃ — 4,101 CH₃ CH₃ O CH₃ X₂ CF₃ — 4,102 CH₃ CH₃ O CH₃ X₃ CF₃ — 4,103 CH₃ CH₃ O CH₃ X₄ CF₃ — 4,104 CH₃ CH₃ O CH₃ X₆ CF₃ — 4,105 CH₃ CH₃ O CH₃ X₁₀ CF₃ — 4,106 CH₃ CH₃ O CH₃ X₁₅ CF₃ — 4,107 CH₃ CH₃ O CH₃ X₂₁ CF₃ — 4,108 CH₃ CH₃ O CH₃ X₂₆ CF₃ — 4,109 CH₃ CH₃ O CH₃ X₃₀ CF₃ — 4,110 CH₃ CH₃ O NO₂ X₁ SO₂CH₃ — 4,111 CH₃ CH₃ O NO₂ X₂ SO₂CH₃ — 4,112 CH₃ CH₃ O NO₂ X₄ SO₂CH₃ — 4,113 CH₃ CH₃ O NO₂ X₂₆ SO₂CH₃ — 4,114 CH₃ CH₃ O NO₂ X₁ CF₃ — 4,115 CH₃ CH₃ O NO₂ X₂ CF₃ — 4,116 CH₃ CH₃ O NO₂ X₄ CF₃ — 4,117 CH₃ CH₃ O NO₂ X₂₆ CF₃ — 4,118 CH₃ C₂H₅ O CH₃ X₁ SO₂CH₃ — 4,119 CH₃ C₂H₅ O CH₃ X₂ SO₂CH₃ — 4,120 CH₃ C₂H₅ O CH₃ X₃ SO₂CH₃ — 4,121 CH₃ C₂H₅ O CH₃ X₄ SO₂CH₃ — 4,122 CH₃ C₂H₅ O CH₃ X₆ SO₂CH₃ — 4,123 CH₃ C₂H₅ O CH₃ X₁₀ SO₂CH₃ — 4,124 CH₃ C₂H₅ O CH₃ X₁₅ SO₂CH₃ — 4,125 CH₃ C₂H₅ O CH₃ X₂₁ SO₂CH₃ — 4,126 CH₃ C₂H₅ O CH₃ X₂₆ SO₂CH₃ — 4,127 CH₃ C₂H₅ O CH₃ X₃₀ SO₂CH₃ — 4,128 C₂H₅ C₂H₅ O CH₃ X₁ SO₂CH₃ — 4,129 C₂H₅ C₂H₅ O CH₃ X₂ SO₂CH₃ — 4,130 C₂H₅ C₂H₅ O CH₃ X₄ SO₂CH₃ — 4,131 C₂H₅ C₂H₅ O CH₃ X₁₀ SO₂CH₃ — 4,132 C₂H₅ C₂H₅ O CH₃ X₁₅ SO₂CH₃ — 4,133 C₂H₅ C₂H₅ O CH₃ X₂₁ SO₂CH₃ — 4,134 C₂H₅ C₂H₅ O CH₃ X₂₆ SO₂CH₃ — 4,135 CH₃ CH₃ O Cl X₁ SCH₃ — 4,136 CH₃ CH₃ O Cl X₂ SCH₃ — 4,137 CH₃ CH₃ O Cl X₃ SCH₃ — 4,138 CH₃ CH₃ O Cl X₄ SCH₃ — 4,139 CH₃ CH₃ O Cl X₅ SCH₃ — 4,140 CH₃ CH₃ O Cl X₆ SCH₃ — 4,141 CH₃ CH₃ O Cl X₇ SCH₃ — 4,142 CH₃ CH₃ O Cl X₁₀ SCH₃ — 4,143 CH₃ CH₃ O Cl X₁₅ SCH₃ — 4,144 CH₃ CH₃ O Cl X₂₀ SCH₃ — 4,145 CH₃ CH₃ O Cl X₂₁ SCH₃ — 4,146 CH₃ CH₃ O Cl X₂₆ SCH₃ — 4,147 CH₃ CH₃ O Cl X₂₇ SCH₃ — 4,148 CH₃ CH₃ O Cl X₂₉ SCH₃ — 4,149 CH₃ CH₃ O Cl X₃₀ SCH₃ — 4,150 CH₃ CH₃ S CH₃ X₁ SO₂CH₃ — 4,151 CH₃ CH₃ S CH₃ X₂ SO₂CH₃ — 4,152 CH₃ CH₃ S CH₃ X₄ SO₂CH₃ — 4,153 CH₃ CH₃ S CH₃ X₂₆ SO₂CH₃ — 4,154 CH₃ CH₃ S Cl X₁ SO₂CH₃ — 4,155 CH₃ CH₃ S Cl X₂ SO₂CH₃ — 4,156 CH₃ CH₃ S Cl X₄ SO₂CH₃ — 4,157 CH₃ CH₃ S Cl X₂₆ SO₂CH₃ — 4,158 CH₃ CH₃ NCH₃ CH₃ X₁ SO₂CH₃ — 4,159 CH₃ CH₃ NCH₃ CH₃ X₂ SO₂CH₃ — 4,160 CH₃ CH₃ NCH₃ CH₃ X₄ SO₂CH₃ — 4,161 CH₃ CH₃ NCH₃ CH₃ X₂₆ SO₂CH₃ — 4,162 H H O CH₃ X₁ SO₂CH₃ — 4,163 H H O CH₃ X₂ SO₂CH₃ — 4,164 H H O CH₃ X₄ SO₂CH₃ — 4,165 H H O CH₃ X₂₆ SO₂CH₃ —

BIOLOGICAL EXAMPLES Example B1 Pre-emergent Herbicidal Action

[0084] Monocot and dicot test plants are sown in standard soil in plastic pots. Immediately after sowing, the plants are sprayed at a concentration of 2 kg active substance/ha with an aqueous suspension of the test compound [prepared from a 25% wettable powder (Example F3, b) in accordance with WO 97/34485] or an emulsion of the test compound [prepared from a 25% emulsifiable concentrate (Example F1 c)] (500 l of water/ha). The test plants are then cultivated in the greenhouse under optimum conditions. The test is evaluated 3 weeks later on a rating scale of 1-9 (1=total damage, 9=no action). Ratings of 1 to 4 (especially of 1 to 3) denote good to very good herbicidal action. TABLE B1 Pre-emergent action: dosage test plant Setaria Cyperus Sinapsis Solanig Stellaria [g AS/ha] Active ingredient No. 1,001 3 3 3 2 2 2000 2,001 3 3 2 2 2 2000

[0085] The same results are obtained by formulating the compounds of formula I in accordance with Examples F2 and F4 to F8 of WO 97/34485.

Example B2 Post-emergent Herbicidal Action

[0086] In a greenhouse, monocot and dicot test plants are sown in standard soil in plastic pots and sprayed in the 4- to 6-leaf stage with an aqueous suspension of the test compounds of formula I prepared from a 25% wettable powder [Example F3, b) of WO 97/34485] or with an emulsion of the test compound of formula I prepared from a 25% emulsifiable concentrate [Example F1 c) of WO 97/34485] at a concentration of 2 kg active substance/ha (500 l of water/ha). The test plants are then further cultivated in the greenhouse under optimum conditions. The test is evaluated about 18 days later on a rating scale of 1-9 (1=total damage, 9=no action). Ratings of 1 to 4 (especially of 1 to 3) denote good to very good herbicidal action. In this test the compounds of formula I exhibit a pronounced herbicidal action. TABLE B2 Post-emergent action: dosage test plant Setaria Cyperus Sinapsis Solanig Stellaria [g AS/ha] Active ingredient No. 1,001 2 3 2 2 2 2000 2,001 3 3 2 2 4 2000

[0087] The same results are obtained by formulating the compounds of formula I in accordance with Examples F2 and F4 to F8 of WO 97/34485. 

1. Compounds of formula I

wherein X is L₁-Y₁-R₄, L₂-Y₂-L₃-Y₃-R₅ or L₄-Y₄-L₅-Y₅-L₆-Y₆-R₆; L₁, L₂, L₃, L₄, L₅, L₆, independently of one another, signify C₁-C₆-alkylene, which may be substituted by C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy, C₂-C₆-alkenyl or C₂-C₆-alkynyl; or C₃-C₆-alkenylene, which may be substituted by C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy, C₂-C₆-alkenyl or C₂-C₆-alkynyl; or C₃-C₆-alkynylene, which may be substituted by C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy, C₂-C₆-alkenyl or C₂-C₆-alkynyl; Y₁, Y₃, Y₆, independently of one another, signify oxygen, sulphur, SO, SO₂, NR₇, OC(O), NR₈SO₂ or OSO₂; Y₂, Y₄, Y₅, independently of one another, signify oxygen, sulphur, SO, SO₂, NR₉, OC(O) or NR₁₀SO₂; R₇, R₈, R₉ and R₁₀, independently of one another, signify hydrogen or C₁-C₆-alkyl; R₁ and R₂, independently of one another, signify halogen, cyano, nitro, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-dialkylaminosulphonyl, C₁-C₆-alkylaminosulphonyl, C₁-C₄-alkylsulphonylamino, C₁-C₆-halogenalkoxy, OSO₂-C₁-C₄-alkyl, C₁-C₆-halogenalkylthio, C₁-C₆-halogenalkylsulphinyl, C₁-C₆-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl; R₃ signifies hydrogen, C₁-C₄-alkyl or halogen; R₄, R₅ and R₆, independently of one another, signify hydrogen, C₁-C₆-alkyl, which may be substituted by the group A₁; C₃-C₇-cycloalkyl, which may be substituted by the group A₂; C₃-C₇-cycloalkyl, which may be interrupted by 1 to 2 oxygen atoms, sulphur or NR₁₁; C₂-C₆-alkenyl, which may be substituted by the group A₃; C₃-C₆-alkynyl, which may be substituted by the group A₄; C₃-C₇-cycloalkyl-C₁-C₄-alkyl, whereby the cycloalkyl group may be interrupted by 1 to 2 oxygen atoms, sulphur or NR₁₂; benzyl or phenyl which may in turn be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, cyano, nitro, C₁-C₄-halogenalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-dialkylamino, C₁-C₄-alkylcarbonyl, C₁-C₄-dialkylaminosulphonyl or NR₁₃-CO-R₁₄; R₁₁ and R₁₂, independently of one another, signify hydrogen or C₁-C₄-alkyl; R₁₃ and R₁₄, independently of one another, signify hydrogen or C₁-C₄-Alkyl; A₁, A₂, A₃, A₄, independently of one another, are hydroxy, formyl, COOH, C₁-C₆-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, OSO₂-C₁-C₄-alkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkylaminocarbonyl, C₁-C₆-dialkylaminocarbonyl, nitro, halogen, cyano, C₁-C₄-alkoxyhalogen, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or phenyl, whereby the phenyl group may in turn be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, cyano, nitro, C₁-C₄-halogenalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-dialkylaminosulphonyl or NR₁₅-CO-R₁₆; R₁₅ and R₁₆, independently of one another, signify hydrogen or C₁-C₄-alkyl; Q is the group Q₁

wherein R₃₉ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-dialkylamino, COOH, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁-C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano; V is C₁-C₄-alkylene, oxygen, sulphur, SO or SO₂; R₁₇, R₁₈, R₁₉, R₂₀, R₂₁ and R₂₂, independently of one another, signify hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkylaminosulphonyl, C₁-C₄-halogenalkyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkoxy, cyano, nitro, halogen or phenyl, q is 1 or 2; or Q is the group Q₂

wherein R₂₃ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-dialkylamino, COOH, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylthio, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphinyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphonyl, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁-C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano; R₂₄ and R₂₅, independently of one another, signify hydrogen, hydroxy, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkylaminosulphonyl, C₁-C₄-halogenalkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, amino, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkyl-S(O)₂O, C₁-C₄-halogenalkylthio, C₁-C₄-halogenalkylsulphinyl, C₁-C₄-halogenalkylsulphonyl, C₁-C₄-halogenalkyl-S(O)₂O, C₁-C₄-alkyl-S(O)₂NH, C₁-C₄-alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or R₂₄ and R₂₅ together form a C₂-C₆-alkylene bridge, R₂₆ signifies hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl or phenyl, which may in turn be substituted by C₁-C₆-alkyl, C₁-C₆-halogenalkyl, C₁-C₆-alkoxy, C₁-C₆-halogenalkoxy, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, amino, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkyl-S(O)₂O, C₁-C₄-halogenalkylthio, C₁-C₄-halogenalkylsulphinyl, C₁-C₄-halogenalkylsulphonyl, C₁-C₄-halogenalkyl-S(O)₂O, C₁-C₄-alkyl-S(O)₂NH, C₁-C₄-alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or Q is the group Q₃

wherein R₂₇ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-dialkylamino, COOH, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylthio, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphinyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphonyl, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁-C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano; R₂₈, R₂₉ and R₄₀, independently of one another, signify hydrogen, hydroxy, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxyoarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkylaminosulphonyl, C₁-C₄-halogenalkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, amino, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkyl-S(O)₂O, C₁-C₄-halogenalkylthio, C₁-C₄-halogenalkylsulphinyl, C₁-C₄-halogenalkylsulphonyl, C₁-C₄-halogenalkyl-S(O)₂O, C₁-C₄-alkyl-S(O)₂NH, C₁-C₄-alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or R₂₈ and R₂₉ together form a C₂-C₆-alkylene bridge, R₃₀ signifies C₁-C₆-alkyl, which may be substituted by a group A₅; C₂-C₆-alkenyl, which may be substituted by a group A₆; C₂-C₆-alkynyl, which may be substituted by a group A₇; A₅, A₆ and A₇, independently of one another, are hydroxy, formyl, COOH, C₁-C₆-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, OSO₂-C₁-C₄-alkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkylaminocarbonyl, C₁-C₆-dialkylaminocarbonyl, nitro, halogen, cyano, C₁-C₄-alkoxyhalogen, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl or phenyl, whereby the phenyl is in turn substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkyl, cyano, nitro, C₁-C₄-halogenalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-dialkylaminosulphonyl or NR₃₁-CO-R₃₂; R₃₁, R₃₂, independently of one another, signify hydrogen or C₁-C₄-alkyl; or Q is the group Q₄

wherein R₃₃ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylthio, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphinyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphonyl, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁-C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano; W is oxygen, sulphur, SO, SO₂, NR₃₈ or C═O; R₃₈ signifies hydrogen or C₁-C₆-alkyl; R₃₄, R₃₅, R₃₆ and R₃₇, independently of one another, signify hydrogen, hydroxy, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkylaminosulphonyl, C₁-C₄-halogenalkyl, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₆-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, amino, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkyl-S(O)₂O, C₁-C₄-halogenalkylthio, C₁-C₄-halogenalkylsulphinyl, C₁-C₄-halogenalkylsulphonyl, C₁-C₄-halogenalkyl-S(O)₂O, C₁-C₄-alkyl-S(O)₂NH, C₁-C₄-alkyl-S(O)₂N(C₁-C₄-alkyl), halogen, nitro, COOH or cyano; or R₃₄ and R₃₅ together form a C₂-C₆-alkylene bridge, as well as agronomically acceptable salts, isomers and enantiomers of these compounds.
 2. Compounds according to 1, whereby R₁ and R₂, independently of one another, signify halogen, cyano, nitro, amino, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-halogenalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₆-dialkylaminosulphonyl, C₁-C₆-alkylaminosulphonyl, C₁-C₆-halogenalkoxy, OSO₂-C₁-C₄-alkyl, C₁-C₆-halogenalkylthio, C₁-C₆-halogen-alkylsulphinyl, C₁-C₆-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl and R₃₃ signifies hydroxy, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyloxy, C₁-C₆-dialkylamino, COOH, C₁-C₆-alkylthio, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylthio, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphinyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkylsulphonyl, C₁-C₆-alkenylthio, C₁-C₆-alkenylsulphinyl, C₁-C₆-alkenylsulphonyl, OSO₂-C₁-C₆-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO₂-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, C₁-C₄-halogenalkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, halogen, nitro, COOH or cyano.
 3. Compounds according to claim 1, whereby Q is Q₁ or Q₂.
 4. Compounds according to claim 1, whereby X is L₁-Y₁-R₄.
 5. Compounds according to claim 4, whereby L₁ signifies methylene.
 6. Compounds according to claim 1, whereby R₂ signifies C₁-C₆-alkylsulphonyl.
 7. A herbicidal and plant growth inhibiting composition, which comprises a herbicidally effective amount of the compound of formula I on an inert carrier.
 8. A method of controlling undesirable plant growth, which comprises treating the plants or the locus thereof with a herbicidally effective amount of a compound of formula I or of a composition containing such a compound.
 9. A method of inhibiting undesirable plant growth, which comprises treating the plants or the locus thereof with a herbicidally effective amount of a compound of formula I or of a composition containing such a compound.
 10. Use of a composition according to claim 7 for controlling undesirable plant growth. 